The National Health Insurance Scheme (NHIS) of Nigeria established in the year 2005 aims to minimize the inequity of access to quality healthcare services in Nigeria. As of the year 2017, enrolment in NHIS-accredited facilities in the southwest region of Nigeria was significantly clustered, with more than three-quarters of NHIS enrollees registered with only 10% of the available NHIS-accredited facilities in the six states of the region. This study explored the factors associated with the skewed distribution of enrollees across facilities and the influence of stakeholders. This is a descriptive, qualitative, case study design among stakeholders of the NHIS in Ibadan, Oyo State, Southwest, Nigeria. In-depth interviews were conducted between March and June, 2019, with all selected individual stakeholders as listed earlier. Data analysis was done using an inductive thematic approach. Across the board, there was a low level of trust in government and government policies among healthcare providers and enrollees. Few healthcare providers were willing to render services under the scheme at inception. The majority of the enrollees were compelled to register with the few available healthcare providers. Among the enrollees, a few personally chose healthcare facilities and providers that were perceived to render better quality services to receive care. Priority should be given to building trust among stakeholders in the NHIS as this would facilitate cooperation and better working relationship, and reposition the scheme for better performance.